6-Chloro-1,2-dihydro-8-methoxy-2-oxopyrrolo<4,3,2-de>quinoline | 157035-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-Chloro-1,2-dihydro-8-methoxy-2-oxopyrrolo<4,3,2-de>quinoline
• 英文别名: 9-Chloro-11-methoxy-2,7-diazatricyclo[6.3.1.04,12]dodeca-1(11),4(12),5,7,9-pentaen-3-one
• CAS: 157035-59-1
• 化学式: C₁₁H₇ClN₂O₂
• 分子量: 234.642
• InChiKey: BMTZZDAYKNYCNW-UHFFFAOYSA-N

物化性质

• 沸点：
  316.6±42.0 °C(predicted)
• 密度：
  1.498±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Chloro-1,2-dihydro-8-methoxy-2-oxopyrrolo<4,3,2-de>quinoline 在 18-冠醚-6 三溴化硼 、 sodium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 336.0h， 以75%的产率得到6-Chloro-1,2-dihydro-8-hydroxy-2-oxopyrrolo<4,3,2-de>quinoline
  参考文献：
  名称：

  Synthesis of Some Pyrrolo[4,3,2-de]quinolines

  摘要：

  The selenium dioxide oxidation of the methyl group in 5-acetamido-6-methoxy-4-methylquinoline produced 1,2-dihydro-8-methoxy-2-oxopyrrolo[4,3,2-de]quinoline, 8b. Halogenation and nitration of 8b gave and 6-substituted derivatives 8c-e. 6-Halo-1,2-dihydro-8-methoxy-2-oxopyrrolo[4,3,2-de]quinolines were O-demethylated, giving phenols 8g and 8h. Reaction of 8b, and its N-methyl derivative 8i, with iodomethane resulted in quaternization of the quinoline ring nitrogen; borohydride reduction of the salts thus produced, and then aerial oxidation, led to dioxindoles 12a,b and 13a,b. Lithium aluminum hydride reduction of 12a produced indole 10b.

  DOI：

  10.1021/jo00095a037
• 作为产物：
  描述：

  6-甲氧基-4-甲基喹啉水合物 在 palladium on activated charcoal sodium hypochlorite 、 selenium(IV) oxide 、 硝酸 、 ammonium formate 作用下， 以 1,4-二氧六环 、 甲醇 、 溶剂黄146 为溶剂， 反应 27.5h， 生成 6-Chloro-1,2-dihydro-8-methoxy-2-oxopyrrolo<4,3,2-de>quinoline
  参考文献：
  名称：

  Synthesis of Some Pyrrolo[4,3,2-de]quinolines

  摘要：

  The selenium dioxide oxidation of the methyl group in 5-acetamido-6-methoxy-4-methylquinoline produced 1,2-dihydro-8-methoxy-2-oxopyrrolo[4,3,2-de]quinoline, 8b. Halogenation and nitration of 8b gave and 6-substituted derivatives 8c-e. 6-Halo-1,2-dihydro-8-methoxy-2-oxopyrrolo[4,3,2-de]quinolines were O-demethylated, giving phenols 8g and 8h. Reaction of 8b, and its N-methyl derivative 8i, with iodomethane resulted in quaternization of the quinoline ring nitrogen; borohydride reduction of the salts thus produced, and then aerial oxidation, led to dioxindoles 12a,b and 13a,b. Lithium aluminum hydride reduction of 12a produced indole 10b.

  DOI：

  10.1021/jo00095a037

文献信息

• Synthesis of Some Pyrrolo[4,3,2-de]quinolines
  作者：Piotr Balczewski、John A. Joule、Carlos Estevez、Mercedes Alvarez

  DOI：10.1021/jo00095a037

  日期：1994.8

  The selenium dioxide oxidation of the methyl group in 5-acetamido-6-methoxy-4-methylquinoline produced 1,2-dihydro-8-methoxy-2-oxopyrrolo[4,3,2-de]quinoline, 8b. Halogenation and nitration of 8b gave and 6-substituted derivatives 8c-e. 6-Halo-1,2-dihydro-8-methoxy-2-oxopyrrolo[4,3,2-de]quinolines were O-demethylated, giving phenols 8g and 8h. Reaction of 8b, and its N-methyl derivative 8i, with iodomethane resulted in quaternization of the quinoline ring nitrogen; borohydride reduction of the salts thus produced, and then aerial oxidation, led to dioxindoles 12a,b and 13a,b. Lithium aluminum hydride reduction of 12a produced indole 10b.